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Synlett 1996; 1996(4): 366-368
DOI: 10.1055/s-1996-5434
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Pd-Catalyzed Alkylation of 1,6-Anhydro-2-chloro-2,3,4-trideoxy-β-D-erythro-hex-3-enopyranose

Masakatsu Matsumoto* , Hiromi Ishikawa, Takayuki Ozawa
  • *Department of Materials Science, Kanagawa University, Tsuchiya, Hiratsuka, Kanagawa 259-12, Japan
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Publication Date:
31 December 2000 (online)

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The palladium(0)-catalyzed substitution of 1,6-anhydro-2-chloro-2,3,4-trideoxy-β-D-erythro-hex-3-enopyranose (2) with active methylene compounds (4a-c) proceeds smoothly to give predominantly 4-substituted products (5) together with 2-isomers (6). The reaction is applied to the synthesis of a key intermediate for thromboxanes and quinuclidinol.

palladium catalyst - levoglucosenone - nucleophilic substitution - alkylation - active methylene compounds - thromboxanes